Like many agents, Segal went to law school, but never intended to find his fortune in the sports world. He was hired by a large "white-shoe" firm out of college, but says he quickly lost interest in the day-to-day grind of life in a big law office.3. This is actually a pretty interesting legal question (NSFW). Via.
So he quit and moved back to his parents house. He had followed the careers of legendary sports agents like Leigh Steinberg and Bob Woolf and decided that was where he wanted to try his hand.
He printed up some business cards with his mother's phone number on them and began cold calling football players. It's not easy for an unknown lawyer with no office and no experience to convince professional athletes to trust him with their financial future. "A lot of guys hung up on me," he says.
Eventually, Segal landed his first client in Brad "Mr. Smooth" Baxter, a little-known running back for the New York Jets. Once he got that first client, however, the doors were opened and it wouldn't take long for other players to come through it.
*Buy sketch cards at eBay.